You know, there was a time when I believed that Leonardo DiCaprio wasn’t a good actor, or at least, I thought he was overrated. In all honesty, I thought that DiCaprio was just in some really good films, and that’s what led people to believe that he was good. But then, I started seeing him in Martin Scorsese movies, and that changed my opinion entirely. Yes, the five Martin Scorsese movies starring DiCaprio are all pretty good, but the truth is, they wouldn’t be nearly as good if Leonardo DiCaprio wasn’t in them, and I think that says a lot about the heavily praised actor.
Now, I already talked about the best Martin Scorsese/Robert De Niro collaborations, so, I wanted to do the same for Leonardo DiCaprio. Granted, the history between DiCaprio and Scorsese doesn’t go all the way back to the ‘70s, like it does for Scorsese and De Niro, but for a time, it felt like DiCaprio truly was Scorsese’s new muse. Interestingly, Scorsese’s next project, Killers of the Flower Moon, will feature both Leonardo DiCaprio AND Robert De Niro, so it’s really the best of both worlds. So, without further ado, here are the best Leonardo DiCaprio performances in Martin Scorsese films, ranked.
Oh, and some major spoilers up ahead.
5. Gangs of New York (Amsterdam Vallon)
In this historical drama, which also stars Daniel Day-Lewis, Cameron Diaz, Liam Neeson, and a whole slew of others, Leonardo DiCaprio plays Amsterdam Vallon, an Irish-American who is seeking vengeance for the murder of his father after a battle broke out concerning the Protestants and the Catholics. DiCaprio’s character infiltrates the rival gang that defeated his father and becomes the head’s right-hand man. This is all in the hopes of one day slaying the man who killed his father. In a lot of ways, Gangs of New York is sort of like The Departed, but with top hats and brogues.
I think it’s a good movie, but here’s the thing - Leonardo DiCaprio’s accent isn’t great. In fact, about halfway through the film, it almost sounds like he drops the accent entirely, only to remember that he’s supposed to have one late in the game, and then pick it back up again in the third act. Plus, it’s kind of hard to shine when you have somebody like Daniel Day-Lewis in the movie acting alongside you. It’s not a bad DiCaprio performance at all. It’s just not nearly as strong as it needed to be.
4. Shutter Island (Edward “Teddy” Daniels/Andrew Laeddis)
In this drama, also starring Michelle Williams, Mark Ruffalo, Ben Kingsley, and Max von Sydow, Leonardo DiCaprio plays two roles, one as the Deputy U.S. Marshal, Edward “Teddy” Daniels, and also as one of an insane asylum’s most dangerous patients, Andrew Laeddis. The most interesting thing about the story though is that (spoiler alert), DiCaprio is essentially hunting himself, as his fractured mind created an alternate alias for himself as a U.S. Marshal as a means of coping for the heinous crime he committed in his everyday life. Riveting stuff.
Leonardo DiCaprio is phenomenal in both roles in this twisty, psychological thriller. The only problem, though, is that Shutter Island is such a phenomenal movie with a brilliant twist ending that you kind of forget how good Leo is in it, because the story itself is the true star of the show. Also, DiCaprio is compelling as both a mentally unhinged man as well as an officer, but probably a lot more compelling as the unhinged man, so it’s not an equal performance.
3. The Wolf of Wall Street (Jordan Belfort)
For a time, Leonardo DiCaprio played almost entirely huggable characters. Titanic was probably the start of a very likable Leo, but I believe it wasn’t until 2012’s Django Unchained and 2013’s The Wolf of Wall Street where he truly shed the nice guy attitude and instead donned a much uglier persona. In the latter instance, he played real life stockbroker Jordan Belfort, where he basically schemed his way to being a playboy rich guy in the late ‘80s, early ‘90s.
The Wolf of Wall Street is all about excess, and what it takes (and the people you have to screw over) in order to be successful. It’s a film that isn’t really professing that greed is good, but rather, that being a prick is good in order to make ridiculous amounts of money, and DiCaprio dials that smugness up to 11. Plus, when he ultimately does get his comeuppance at the end, you don’t really feel like he even learned his lesson. He’s like a very charming version of Alex DeLarge from A Clockwork Orange, minus the violence, and anybody who can pull that off is aces in my book.
2. The Aviator (Howard Hughes)
“Wave of the future. Wave of the future.” The Aviator is a biopic about Howard Hughes, and his literal ups and downs as a movie director and airplane pilot, and ultimately, his succumbing to his own extreme OCD. We see DiCaprio in so many different forms in this excellently paced and well-crafted movie, that we feel both sympathy for him, but also a bit of disdain for his jealous streak and even his quirks. The Aviator is one for the ages.
And here’s the thing. Unlike with Shutter Island, where we abruptly find out that the stable hero we’ve been following for most of the movie isn’t so stable after all, we always see hints of the ultimate decline in Howard Hughes’ character throughout The Aviator. It’s the kind of performance where there is always something lurking beneath the surface, and for Leo to maintain that for so long before he goes full on OCD, is a testament to how truly good he is as an actor.
1. The Departed (Trooper William “Billy” Costigan Jr.)
The Departed stars pretty much everybody under the sun, including Jack Nicholson, Vera Farmiga, Matt Damon, Martin Sheen, and several others. And, while many will probably say that Matt Damon is the brain of this twisty crime drama, Leonardo DiCaprio, as the cop who infiltrates the Irish Mob, is undoubtedly the bloody beating heart.
Throughout the film, there is a constant sense of dread about whether Matt Damon’s character will get caught within the police system as a mole, or whether DiCaprio’s undercover character will get caught by the mob, but the audience knows that DiCaprio’s character is always the one who has the deadlier assignment. It is through this nervousness that we get completely enraptured in this story, which wouldn’t be possible if Leo didn’t personify this nervousness to a T.
It’s rare where you feel anxious while watching a movie, but you do with The Departed, and I think it all goes back to DiCaprio's unbelievable performance. I know that he ultimately earned his Oscar for The Revenant, and that he was nominated in the same year as The Departed for his performance in Blood Diamond, but I honestly think that his performance as William “Billy” Costigan in The Departed should have been the one he was nominated for, as it’s probably my favorite performance of his.
If you want to read about the best Leonardo DiCaprio movies of all time or other pieces on him, then make sure to swing by here often.
